I recently was a guest on the Strong Suit Podcast, discussing habits of successful and unsuccessful boards of directors. I compressed learning from 16 years and 750+ board meetings into 22 minutes! Enjoy.

I’ve been a Cubs fan for 20 years. It’s the first team I adopted when I moved to Chicago after college. I realize that’s not a lifetime, but I’m emotionally invested. It is for this reason that the World Series run up was thrilling and scary all at the same time. It’s magnified because I live right off of Addison St. a mile and a half from Wrigley.

There are so many lessons on teamwork in this victory: players that committed errors in the field only to follow it with a homerun at their next at bat. Recovering from disappointment and mistakes with resiliency. This is a team that relied on team depth and did not have reliance on any one player. It reminds me of the great Bo Schembechler speech (excerpts below):

This story is about a good friend of mine who wished to remain anonymous given the content of the story. We wrote this story together. Enjoy.

It was an unusually crummy weather day in 2005, and my wife and I decided to go to a movie.

As we were exiting our parked car to go into the theater, my wife inquired if she had to bring along her big purse. I’m always amazed on the occasions that I have to lift it. It is so heavy, I once checked if it contained a boulder collection or several preschool children.

“Naaaah, leave the purse,” I said. My thinking: this was a pretty safe part of the city, and she didn’t need her purse in the theater and who wants to schlep a heavy purse for no reason?

The movie turned out to be awful, and we talked about the chain of bad decisions that resulted in the production of this opposite-of-a-masterpiece. Little did we know that this conversation would be a foreshadow. Read More

In 2014, Nick Kokonas wrote a manifesto highlighting that if restaurants used tickets instead of free reservations, restaurants could dramatically reduce no-shows, optimize their supply chains, improve working capital, and eliminate staff answering the phones to take reservations. It made so much sense– the world SHOULD work that way, but it does not. It prompted the question: why are consumers willing to buy a ticket for a performance but not for a restaurant? Are consumers willing to change this behavior? Could Tock help restaurants– notoriously difficult businesses– dramatically improve operations and financial results? Read More

I’ve been through two severe market declines, both in 2001 and 2009. Public market volatility at the beginning of 2016 gave birth to a lot of “doom and gloom” posts on VC blogs. The public markets have recovered, but the scare earlier this year seems to have resulted in more conservative cash planning within early stage companies. Investors and founders alike are paying closer attention to multiples. It also got VCs like me thinking more about structure.

There is a large wave of companies that raised capital in the last 18-24 months that will come to market for capital soon or have recently done so. The key obstacle for these companies is that they likely raised capital at a valuation higher than they could retrieve in the markets today. These companies might have made substantial progress in their businesses, thereby reducing the risk, and therefore increasing the valuation….or so the argument goes. The issue, however, is that the price for unit of risk has gone down. In other words, there is a generation of companies that need to accomplish significant traction just to earn their most recent valuation. I’ve heard several people recently proclaim “flat is the new up round.” Read More

I am not much of a student of history. I do, however, believe it’s important to honor the previous generations for the contributions and sacrifices that give rise to the current generation. I’ve always liked Newton’s quote: “If I have seen further it is by standing on the shoulders of giants.”

The history of Origin Ventures is rooted in the success of the Quill office products company. It was started by two brothers who built it for 47 years before it was acquired by Staples. The success of Quill made Origin Ventures possible.

When we moved into our new Origin offices in January, we had a lot of wall space to fill. In addition to not being a student of history, I am also not a student of art (perhaps there is a correlation). Lacking instincts in selecting art, combined with the high cost of art, is not a good combination. As a result, I thought there might be a way to make our own art that was cheap. Furthermore, I felt it would be meaningful to use art in a way to tie Quill to Origin somehow.

It’s been really exciting to watch the explosion of startup activity the last three years. This expansion has been characterized by technology infrastructure shifting from fixed cost to variable, proliferation of seed funds and accelerator programs, exit markets opening and other factors.

A byproduct of this increase in seed investment activity is the wide use of convertible notes. I am all for structural innovation, but I believe that the use of convertible notes has drifted away from the original purpose, and this shift is a bad thing for founder and investor alike.